NPASS Compound

Structure

CID326363 OpenBabel06191716192D 95101 0 0 1 0 0 0 0 0999 V2000 -3.0630 -2.8164 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2219 -4.1036 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.7132 1.6826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.8942 3.4052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1194 10.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7811 -2.3963 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6237 9.3359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0705 9.6960 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3744 -1.4827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1933 -3.2053 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3044 4.7456 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4089 5.7402 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6447 -1.6473 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4158 8.3577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2784 8.7178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3799 -1.3782 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1988 -3.1007 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3909 4.3389 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5999 6.3280 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.8526 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5388 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6973 7.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4293 7.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.6973 8.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.4293 8.5924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9071 8.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9016 8.5886 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6937 -1.9563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 -0.8090 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7572 -2.4563 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7431 7.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5633 6.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2024 -2.0827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1970 3.8052 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3523 8.8577 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1037 5.5848 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0140 -3.1254 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3065 2.5962 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5352 8.0487 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2079 -2.1872 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5633 7.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6037 4.7188 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5633 9.0924 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5818 4.9267 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6864 5.9212 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1095 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.5003 7.5706 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.5493 -1.4781 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0000 6.4014 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.6973 5.5924 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 1.2024 3.7007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.5602 7.8796 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6092 -1.1691 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5878 0.8090 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -7.3083 9.5022 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0955 9.5268 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3119 2.7007 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -6.3664 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3664 7.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5547 -1.5827 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 7.0706 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 4.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5547 7.9841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1040 4.6789 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9945 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1040 1.7226 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7431 -0.6691 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4858 -2.9344 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.3028 9.6067 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0465 9.2178 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7728 6.3280 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.5493 7.8796 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.6973 0.8090 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -5.5003 -1.1691 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -7.1095 6.4014 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.5878 5.5924 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6092 7.5706 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.2024 2.7007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5602 -1.4781 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.3119 3.7007 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -8.5633 10.0924 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.7205 10.3112 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8875 10.5050 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9541 -1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.9541 7.8796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5547 -2.5827 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1554 7.8796 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 4.9879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5547 8.9841 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0551 4.9879 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9456 1.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.0551 1.4135 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.1554 -1.4781 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 38 1 0 0 0 0 2 38 1 0 0 0 0 3 39 1 0 0 0 0 4 39 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 17 1 0 0 0 0 10 18 2 0 0 0 0 11 12 2 0 0 0 0 11 19 1 0 0 0 0 12 20 1 0 0 0 0 13 21 1 0 0 0 0 13 29 1 0 0 0 0 14 22 1 0 0 0 0 14 30 1 0 0 0 0 15 40 2 0 0 0 0 16 40 1 0 0 0 0 17 41 2 0 0 0 0 18 41 1 0 0 0 0 19 45 2 0 0 0 0 20 46 2 0 0 0 0 23 25 1 0 0 0 0 23 42 2 0 0 0 0 24 26 2 0 0 0 0 24 42 1 0 0 0 0 25 44 2 0 0 0 0 26 44 1 0 0 0 0 27 28 1 0 0 0 0 28 56 1 0 0 0 0 29 69 1 0 0 0 0 30 82 1 0 0 0 0 31 38 1 0 0 0 0 32 40 1 0 0 0 0 33 42 1 0 0 0 0 34 41 1 0 0 0 0 35 43 1 0 0 0 0 36 57 1 0 0 0 0 37 43 2 0 0 0 0 37 72 1 0 0 0 0 43 45 1 0 0 0 0 44 83 1 0 0 0 0 45 46 1 0 0 0 0 46 72 1 0 0 0 0 47 21 1 6 0 0 0 47 59 1 0 0 0 0 47 74 1 0 0 0 0 48 27 1 6 0 0 0 48 60 1 0 0 0 0 48 73 1 0 0 0 0 49 31 1 6 0 0 0 49 61 1 0 0 0 0 49 75 1 0 0 0 0 50 32 1 1 0 0 0 50 62 1 0 0 0 0 50 77 1 0 0 0 0 51 33 1 6 0 0 0 51 65 1 0 0 0 0 51 76 1 0 0 0 0 52 35 1 6 0 0 0 52 63 1 0 0 0 0 52 79 1 0 0 0 0 53 36 1 6 0 0 0 53 64 1 0 0 0 0 53 78 1 0 0 0 0 54 34 1 1 0 0 0 54 68 1 0 0 0 0 54 80 1 0 0 0 0 55 22 1 6 0 0 0 55 66 1 0 0 0 0 55 82 1 0 0 0 0 56 70 2 0 0 0 0 56 84 1 0 0 0 0 57 71 2 0 0 0 0 57 85 1 0 0 0 0 58 39 1 6 0 0 0 58 67 1 0 0 0 0 58 81 1 0 0 0 0 59 75 2 3 0 0 0 59 86 1 0 0 0 0 60 76 2 3 0 0 0 60 87 1 0 0 0 0 61 80 2 3 0 0 0 61 88 1 0 0 0 0 62 78 2 3 0 0 0 62 89 1 0 0 0 0 63 77 2 3 0 0 0 63 90 1 0 0 0 0 64 73 2 3 0 0 0 64 91 1 0 0 0 0 65 81 2 3 0 0 0 65 92 1 0 0 0 0 66 79 2 3 0 0 0 66 93 1 0 0 0 0 67 74 2 3 0 0 0 67 94 1 0 0 0 0 68 82 1 0 0 0 0 68 95 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	1308.67
Volume:	1327.104
LogP:	1.73
LogD:	1.781
LogS:	-2.968
# Rotatable Bonds:	19
TPSA:	453.35
# H-Bond Aceptor:	27
# H-Bond Donor:	17
# Rings:	7
# Heavy Atoms:	27

MedChem Properties

QED Drug-Likeness Score:	0.029
Synthetic Accessibility Score:	7.44
Fsp3:	0.441
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-3.23
MDCK Permeability:	0.00019883700588252395
Pgp-inhibitor:	0.032
Pgp-substrate:	1.0
Human Intestinal Absorption (HIA):	0.999
20% Bioavailability (F20%):	0.996
30% Bioavailability (F30%):	0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.853
Plasma Protein Binding (PPB):	47.79159164428711%
Volume Distribution (VD):	0.513
Pgp-substrate:	39.29549026489258%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.011
CYP2C19-substrate:	0.022
CYP2C9-inhibitor:	0.037
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.007
CYP2D6-substrate:	0.046
CYP3A4-inhibitor:	0.091
CYP3A4-substrate:	0.003

ADMET: Excretion

Clearance (CL):	0.566
Half-life (T1/2):	0.847

ADMET: Toxicity

hERG Blockers:	0.0
Human Hepatotoxicity (H-HT):	1.0
Drug-inuced Liver Injury (DILI):	0.989
AMES Toxicity:	0.005
Rat Oral Acute Toxicity:	0.284
Maximum Recommended Daily Dose:	0.919
Skin Sensitization:	0.788
Carcinogencity:	0.287
Eye Corrosion:	0.003
Eye Irritation:	0.005
Respiratory Toxicity:	0.951

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC326363

Natural Product ID:	NPC326363
*Common Name:**	Tyrocidine B
IUPAC Name:	3-[(3R,6S,9S,12S,15S,18S,21S,24R,27S,30S)-21-(2-amino-2-oxoethyl)-9-(3-aminopropyl)-3,24-dibenzyl-15-[(4-hydroxyphenyl)methyl]-27-(1H-indol-3-ylmethyl)-6-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29-decaoxo-12-propan-2-yl-1,4,7,10,13,16,19,22,25,28-decazabicyclo[28.3.0]tritriacontan-18-yl]propanamide
Synonyms:
Standard InCHIKey:	PUVWPDQSNYAMEH-UQHIYWQBSA-N
Standard InCHI:	InChI=1S/C68H88N14O13/c1-38(2)31-49-61(88)80-54(34-41-17-9-6-10-18-41)68(95)82-30-14-22-55(82)66(93)79-52(35-43-37-72-46-20-12-11-19-45(43)46)63(90)77-50(32-40-15-7-5-8-16-40)62(89)78-53(36-57(71)85)64(91)73-48(27-28-56(70)84)60(87)76-51(33-42-23-25-44(83)26-24-42)65(92)81-58(39(3)4)67(94)74-47(21-13-29-69)59(86)75-49/h5-12,15-20,23-26,37-39,47-55,58,72,83H,13-14,21-22,27-36,69H2,1-4H3,(H2,70,84)(H2,71,85)(H,73,91)(H,74,94)(H,75,86)(H,76,87)(H,77,90)(H,78,89)(H,79,93)(H,80,88)(H,81,92)/t47-,48-,49-,50+,51-,52-,53-,54+,55-,58-/m0/s1
SMILES:	NCCC[C@@H]1N=C(O)[C@@H](N=C(O)[C@H](Cc2ccc(cc2)O)N=C(O)[C@H](CCC(=N)O)N=C(O)[C@H](CC(=N)O)N=C(O)[C@H](N=C([C@@H](N=C([C@H]2N(C(=O)[C@H](N=C([C@@H](N=C1O)CC(C)C)O)Cc1ccccc1)CCC2)O)Cc1c[nH]c2c1cccc2)O)Cc1ccccc1)C(C)C
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL568927
PubChem CID:	16160723
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000264] Organic acids and derivatives [CHEMONTID:0000265] Carboxylic acids and derivatives [CHEMONTID:0000013] Amino acids, peptides, and analogues [CHEMONTID:0000348] Peptides [CHEMONTID:0004831] Oligopeptides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO23673	Brevibacillus brevis	Species	Paenibacillaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4320358]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	3
Others	7

Activity Type	# Activity
NON-MOLECULAR	1
Organism	9

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Activity	<	50.0	%	PMID[483486]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Activity	=	1.53	%	PMID[483486]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	Activity	=	64.0	%	PMID[483486]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	T1/2	=	0.48	hr	PMID[483486]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	IC50	=	6500.0	nM	PMID[483486]
NPT729	Organism	Micrococcus luteus	Micrococcus luteus	ICmax	=	9.9	uM	PMID[483486]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	IC50	=	10000.0	nM	PMID[483486]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	ICmax	=	15.0	uM	PMID[483486]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	IC50	=	7700.0	nM	PMID[483486]
NPT564	Organism	Listeria monocytogenes	Listeria monocytogenes	ICmax	=	12.0	uM	PMID[483486]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC326363 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	446
0.1-0.2	2238
0.2-0.3	14094
0.3-0.4	12165
0.4-0.5	8034
0.5-0.6	2989
0.6-0.7	2089
0.7-0.8	553
0.8-0.85	71
0.85-0.9	12
0.9-0.95	3
0.95-1	3

Similarity Score	Similarity Level	Natural Product ID
0.9807	High Similarity	NPC325976
0.9013	High Similarity	NPC153400
0.892	High Similarity	NPC24370
0.892	High Similarity	NPC319232
0.8813	High Similarity	NPC28945
0.8676	High Similarity	NPC323752
0.8559	High Similarity	NPC285343
0.8531	High Similarity	NPC75634
0.8478	Intermediate Similarity	NPC314882
0.8423	Intermediate Similarity	NPC220852
0.8412	Intermediate Similarity	NPC478006
0.8364	Intermediate Similarity	NPC478157
0.8319	Intermediate Similarity	NPC478009
0.8303	Intermediate Similarity	NPC473317
0.8302	Intermediate Similarity	NPC162860
0.8294	Intermediate Similarity	NPC54420
0.8278	Intermediate Similarity	NPC155143
0.8277	Intermediate Similarity	NPC315467
0.8249	Intermediate Similarity	NPC477714
0.8249	Intermediate Similarity	NPC264285
0.8235	Intermediate Similarity	NPC214142
0.823	Intermediate Similarity	NPC475506
0.823	Intermediate Similarity	NPC184225
0.8227	Intermediate Similarity	NPC213629
0.8221	Intermediate Similarity	NPC100321
0.8214	Intermediate Similarity	NPC321592
0.8214	Intermediate Similarity	NPC54803
0.8206	Intermediate Similarity	NPC95240
0.8206	Intermediate Similarity	NPC223409
0.8203	Intermediate Similarity	NPC477715
0.8198	Intermediate Similarity	NPC124920
0.8198	Intermediate Similarity	NPC118559
0.8198	Intermediate Similarity	NPC34580
0.8198	Intermediate Similarity	NPC304307
0.8198	Intermediate Similarity	NPC261251
0.819	Intermediate Similarity	NPC477630
0.819	Intermediate Similarity	NPC125597
0.819	Intermediate Similarity	NPC477635
0.8186	Intermediate Similarity	NPC75726
0.8186	Intermediate Similarity	NPC110602
0.8186	Intermediate Similarity	NPC31385
0.8173	Intermediate Similarity	NPC473640
0.8173	Intermediate Similarity	NPC171317
0.8167	Intermediate Similarity	NPC478010
0.8161	Intermediate Similarity	NPC100547
0.8131	Intermediate Similarity	NPC478158
0.8125	Intermediate Similarity	NPC322135
0.81	Intermediate Similarity	NPC16352
0.8089	Intermediate Similarity	NPC14288
0.8082	Intermediate Similarity	NPC281049
0.8072	Intermediate Similarity	NPC477633
0.8056	Intermediate Similarity	NPC320968
0.8048	Intermediate Similarity	NPC293917
0.8047	Intermediate Similarity	NPC223791
0.8047	Intermediate Similarity	NPC107077
0.8039	Intermediate Similarity	NPC94752
0.8035	Intermediate Similarity	NPC41679
0.8019	Intermediate Similarity	NPC99666
0.8018	Intermediate Similarity	NPC284888
0.8018	Intermediate Similarity	NPC323198
0.8009	Intermediate Similarity	NPC315491
0.8009	Intermediate Similarity	NPC45459
0.8008	Intermediate Similarity	NPC314056
0.8	Intermediate Similarity	NPC478011
0.8	Intermediate Similarity	NPC303658
0.7982	Intermediate Similarity	NPC33064
0.7982	Intermediate Similarity	NPC245055
0.7967	Intermediate Similarity	NPC314176
0.7957	Intermediate Similarity	NPC82472
0.7955	Intermediate Similarity	NPC304926
0.7955	Intermediate Similarity	NPC476041
0.7944	Intermediate Similarity	NPC473376
0.7913	Intermediate Similarity	NPC17059
0.791	Intermediate Similarity	NPC478013
0.7867	Intermediate Similarity	NPC156704
0.786	Intermediate Similarity	NPC470500
0.786	Intermediate Similarity	NPC475070
0.7854	Intermediate Similarity	NPC478012
0.7854	Intermediate Similarity	NPC473312
0.785	Intermediate Similarity	NPC476874
0.7848	Intermediate Similarity	NPC276657
0.7847	Intermediate Similarity	NPC324149
0.7845	Intermediate Similarity	NPC477861
0.7826	Intermediate Similarity	NPC46580
0.7817	Intermediate Similarity	NPC328924
0.7798	Intermediate Similarity	NPC476116
0.7797	Intermediate Similarity	NPC323244
0.7797	Intermediate Similarity	NPC6215
0.7792	Intermediate Similarity	NPC478028
0.7788	Intermediate Similarity	NPC321708
0.7778	Intermediate Similarity	NPC171171
0.7767	Intermediate Similarity	NPC228835
0.7767	Intermediate Similarity	NPC193761
0.7763	Intermediate Similarity	NPC56109
0.7763	Intermediate Similarity	NPC191382
0.7763	Intermediate Similarity	NPC194740
0.7763	Intermediate Similarity	NPC5145
0.7759	Intermediate Similarity	NPC15801
0.7748	Intermediate Similarity	NPC74969
0.7748	Intermediate Similarity	NPC183407
0.7739	Intermediate Similarity	NPC89987
0.7739	Intermediate Similarity	NPC207686
0.7738	Intermediate Similarity	NPC54744
0.7731	Intermediate Similarity	NPC476098
0.7729	Intermediate Similarity	NPC314002
0.7725	Intermediate Similarity	NPC478029
0.7725	Intermediate Similarity	NPC470784
0.7719	Intermediate Similarity	NPC476491
0.7716	Intermediate Similarity	NPC477549
0.7714	Intermediate Similarity	NPC473763
0.7714	Intermediate Similarity	NPC117244
0.7713	Intermediate Similarity	NPC27041
0.7713	Intermediate Similarity	NPC305984
0.7707	Intermediate Similarity	NPC271792
0.7706	Intermediate Similarity	NPC323927
0.77	Intermediate Similarity	NPC77555
0.7682	Intermediate Similarity	NPC184680
0.7681	Intermediate Similarity	NPC204717
0.7674	Intermediate Similarity	NPC213308
0.7668	Intermediate Similarity	NPC322064
0.7664	Intermediate Similarity	NPC131887
0.7664	Intermediate Similarity	NPC306376
0.7655	Intermediate Similarity	NPC474896
0.765	Intermediate Similarity	NPC470785
0.7644	Intermediate Similarity	NPC15102
0.7644	Intermediate Similarity	NPC269270
0.7644	Intermediate Similarity	NPC313804
0.7644	Intermediate Similarity	NPC315804
0.7639	Intermediate Similarity	NPC272549
0.7637	Intermediate Similarity	NPC78609
0.7636	Intermediate Similarity	NPC61038
0.7635	Intermediate Similarity	NPC314603
0.7633	Intermediate Similarity	NPC220765
0.7632	Intermediate Similarity	NPC476818
0.7627	Intermediate Similarity	NPC171393
0.7627	Intermediate Similarity	NPC295452
0.7626	Intermediate Similarity	NPC270918
0.7621	Intermediate Similarity	NPC31097
0.7621	Intermediate Similarity	NPC155444
0.7619	Intermediate Similarity	NPC475969
0.7619	Intermediate Similarity	NPC475859
0.7619	Intermediate Similarity	NPC476451
0.7617	Intermediate Similarity	NPC227582
0.7613	Intermediate Similarity	NPC475746
0.7611	Intermediate Similarity	NPC272174
0.7611	Intermediate Similarity	NPC14686
0.761	Intermediate Similarity	NPC477634
0.7609	Intermediate Similarity	NPC33949
0.7605	Intermediate Similarity	NPC178858
0.76	Intermediate Similarity	NPC473310
0.7594	Intermediate Similarity	NPC471448
0.7593	Intermediate Similarity	NPC252338
0.7588	Intermediate Similarity	NPC64216
0.758	Intermediate Similarity	NPC175602
0.7578	Intermediate Similarity	NPC477610
0.7576	Intermediate Similarity	NPC477175
0.7576	Intermediate Similarity	NPC470730
0.7576	Intermediate Similarity	NPC69843
0.7573	Intermediate Similarity	NPC11126
0.7568	Intermediate Similarity	NPC82370
0.7566	Intermediate Similarity	NPC193267
0.7566	Intermediate Similarity	NPC213530
0.7565	Intermediate Similarity	NPC186351
0.7558	Intermediate Similarity	NPC300183
0.7552	Intermediate Similarity	NPC181081
0.7545	Intermediate Similarity	NPC88008
0.7543	Intermediate Similarity	NPC474877
0.7542	Intermediate Similarity	NPC91868
0.7542	Intermediate Similarity	NPC63971
0.7536	Intermediate Similarity	NPC91179
0.7534	Intermediate Similarity	NPC153980
0.7534	Intermediate Similarity	NPC6865
0.7534	Intermediate Similarity	NPC110182
0.7524	Intermediate Similarity	NPC59269
0.7512	Intermediate Similarity	NPC249040
0.7512	Intermediate Similarity	NPC470497
0.7511	Intermediate Similarity	NPC330009
0.7511	Intermediate Similarity	NPC477516
0.7511	Intermediate Similarity	NPC81175
0.7511	Intermediate Similarity	NPC165743
0.7511	Intermediate Similarity	NPC63031
0.7511	Intermediate Similarity	NPC170114
0.75	Intermediate Similarity	NPC60621
0.75	Intermediate Similarity	NPC470729
0.75	Intermediate Similarity	NPC101350
0.75	Intermediate Similarity	NPC207866
0.75	Intermediate Similarity	NPC266931
0.75	Intermediate Similarity	NPC477176
0.7489	Intermediate Similarity	NPC72956
0.7489	Intermediate Similarity	NPC53144
0.748	Intermediate Similarity	NPC117980
0.7479	Intermediate Similarity	NPC63279
0.7478	Intermediate Similarity	NPC472285
0.7468	Intermediate Similarity	NPC477177
0.7467	Intermediate Similarity	NPC162748
0.7467	Intermediate Similarity	NPC220851
0.7467	Intermediate Similarity	NPC470549
0.7466	Intermediate Similarity	NPC183777
0.7458	Intermediate Similarity	NPC235685
0.7457	Intermediate Similarity	NPC253580

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC326363 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	227
0.1-0.2	554
0.2-0.3	868
0.3-0.4	1435
0.4-0.5	2557
0.5-0.6	2362
0.6-0.7	1005
0.7-0.8	135
0.8-0.85	5
0.85-0.9	1
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9507	High Similarity	NPD8405	Clinical (unspecified phase)
0.8657	High Similarity	NPD7603	Discontinued
0.8571	High Similarity	NPD7948	Phase 1
0.8357	Intermediate Similarity	NPD8093	Discontinued
0.8294	Intermediate Similarity	NPD8493	Clinical (unspecified phase)
0.8224	Intermediate Similarity	NPD7470	Discontinued
0.8148	Intermediate Similarity	NPD8094	Discontinued
0.8122	Intermediate Similarity	NPD6838	Clinical (unspecified phase)
0.8048	Intermediate Similarity	NPD7621	Clinical (unspecified phase)
0.8037	Intermediate Similarity	NPD7823	Clinical (unspecified phase)
0.8009	Intermediate Similarity	NPD484	Approved
0.7955	Intermediate Similarity	NPD8406	Clinical (unspecified phase)
0.7926	Intermediate Similarity	NPD7998	Clinical (unspecified phase)
0.7895	Intermediate Similarity	NPD5575	Clinical (unspecified phase)
0.786	Intermediate Similarity	NPD5040	Clinical (unspecified phase)
0.786	Intermediate Similarity	NPD8272	Phase 2
0.7857	Intermediate Similarity	NPD7944	Discontinued
0.7844	Intermediate Similarity	NPD7809	Clinical (unspecified phase)
0.7808	Intermediate Similarity	NPD8013	Clinical (unspecified phase)
0.7783	Intermediate Similarity	NPD7951	Approved
0.7783	Intermediate Similarity	NPD7790	Approved
0.7783	Intermediate Similarity	NPD7953	Approved
0.7783	Intermediate Similarity	NPD7950	Approved
0.7783	Intermediate Similarity	NPD7791	Approved
0.7783	Intermediate Similarity	NPD7789	Approved
0.7783	Intermediate Similarity	NPD7952	Approved
0.7778	Intermediate Similarity	NPD6824	Clinical (unspecified phase)
0.7763	Intermediate Similarity	NPD7781	Approved
0.7763	Intermediate Similarity	NPD7780	Approved
0.7734	Intermediate Similarity	NPD8349	Phase 1
0.7703	Intermediate Similarity	NPD7971	Clinical (unspecified phase)
0.7703	Intermediate Similarity	NPD7970	Approved
0.7692	Intermediate Similarity	NPD7594	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD2916	Discontinued
0.7661	Intermediate Similarity	NPD7958	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD7957	Phase 1
0.7656	Intermediate Similarity	NPD6141	Clinical (unspecified phase)
0.7656	Intermediate Similarity	NPD8431	Approved
0.7642	Intermediate Similarity	NPD8284	Discontinued
0.7642	Intermediate Similarity	NPD7731	Approved
0.7642	Intermediate Similarity	NPD7730	Approved
0.7615	Intermediate Similarity	NPD5426	Phase 3
0.7591	Intermediate Similarity	NPD7947	Clinical (unspecified phase)
0.7589	Intermediate Similarity	NPD5612	Discontinued
0.7576	Intermediate Similarity	NPD7824	Approved
0.757	Intermediate Similarity	NPD6449	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD8430	Approved
0.7565	Intermediate Similarity	NPD8292	Phase 2
0.756	Intermediate Similarity	NPD6344	Clinical (unspecified phase)
0.7556	Intermediate Similarity	NPD8000	Clinical (unspecified phase)
0.7555	Intermediate Similarity	NPD7271	Approved
0.7554	Intermediate Similarity	NPD7558	Phase 2
0.7548	Intermediate Similarity	NPD2092	Phase 2
0.7548	Intermediate Similarity	NPD2094	Phase 2
0.7548	Intermediate Similarity	NPD2095	Phase 2
0.7548	Intermediate Similarity	NPD5728	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD8112	Clinical (unspecified phase)
0.7544	Intermediate Similarity	NPD8356	Approved
0.7542	Intermediate Similarity	NPD8017	Clinical (unspecified phase)
0.7542	Intermediate Similarity	NPD8016	Phase 3
0.7536	Intermediate Similarity	NPD8110	Clinical (unspecified phase)
0.7523	Intermediate Similarity	NPD7619	Phase 3
0.7523	Intermediate Similarity	NPD7618	Phase 3
0.7522	Intermediate Similarity	NPD8289	Discontinued
0.7522	Intermediate Similarity	NPD7711	Discontinued
0.7512	Intermediate Similarity	NPD2096	Phase 2
0.7512	Intermediate Similarity	NPD2091	Phase 2
0.7511	Intermediate Similarity	NPD4885	Approved
0.7511	Intermediate Similarity	NPD7666	Phase 3
0.7511	Intermediate Similarity	NPD7665	Phase 2
0.7466	Intermediate Similarity	NPD8322	Phase 2
0.7465	Intermediate Similarity	NPD6999	Discontinued
0.7465	Intermediate Similarity	NPD7000	Clinical (unspecified phase)
0.7465	Intermediate Similarity	NPD8396	Approved
0.7465	Intermediate Similarity	NPD8395	Approved
0.7455	Intermediate Similarity	NPD7712	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD6595	Phase 3
0.7427	Intermediate Similarity	NPD5065	Approved
0.7421	Intermediate Similarity	NPD7001	Phase 3
0.7395	Intermediate Similarity	NPD802	Phase 2
0.7393	Intermediate Similarity	NPD6610	Clinical (unspecified phase)
0.7383	Intermediate Similarity	NPD7181	Phase 3
0.7382	Intermediate Similarity	NPD5559	Phase 2
0.738	Intermediate Similarity	NPD6242	Discontinued
0.7376	Intermediate Similarity	NPD5901	Discontinued
0.7368	Intermediate Similarity	NPD8464	Clinical (unspecified phase)
0.7366	Intermediate Similarity	NPD4184	Clinical (unspecified phase)
0.7364	Intermediate Similarity	NPD8073	Approved
0.7357	Intermediate Similarity	NPD6803	Clinical (unspecified phase)
0.7356	Intermediate Similarity	NPD6203	Clinical (unspecified phase)
0.7354	Intermediate Similarity	NPD6376	Discontinued
0.7349	Intermediate Similarity	NPD6665	Discontinued
0.7343	Intermediate Similarity	NPD482	Approved
0.7342	Intermediate Similarity	NPD4862	Clinical (unspecified phase)
0.7339	Intermediate Similarity	NPD4845	Discontinued
0.733	Intermediate Similarity	NPD8072	Approved
0.7321	Intermediate Similarity	NPD8524	Approved
0.7317	Intermediate Similarity	NPD8247	Approved
0.7317	Intermediate Similarity	NPD8246	Approved
0.7315	Intermediate Similarity	NPD1038	Approved
0.7308	Intermediate Similarity	NPD749	Clinical (unspecified phase)
0.7296	Intermediate Similarity	NPD7426	Phase 1
0.7292	Intermediate Similarity	NPD7576	Discontinued
0.729	Intermediate Similarity	NPD6965	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7825	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD6975	Discontinued
0.7273	Intermediate Similarity	NPD5483	Clinical (unspecified phase)
0.7265	Intermediate Similarity	NPD6165	Phase 2
0.7265	Intermediate Similarity	NPD6164	Phase 2
0.7258	Intermediate Similarity	NPD8091	Phase 3
0.7246	Intermediate Similarity	NPD8106	Phase 2
0.724	Intermediate Similarity	NPD4511	Phase 1
0.724	Intermediate Similarity	NPD7903	Clinical (unspecified phase)
0.7233	Intermediate Similarity	NPD7393	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD8458	Clinical (unspecified phase)
0.7224	Intermediate Similarity	NPD5482	Discontinued
0.722	Intermediate Similarity	NPD8114	Approved
0.722	Intermediate Similarity	NPD8115	Approved
0.7216	Intermediate Similarity	NPD7689	Approved
0.7212	Intermediate Similarity	NPD750	Phase 2
0.7197	Intermediate Similarity	NPD7853	Phase 2
0.7193	Intermediate Similarity	NPD8488	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD3243	Approved
0.7188	Intermediate Similarity	NPD6732	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7203	Clinical (unspecified phase)
0.7182	Intermediate Similarity	NPD7777	Approved
0.7182	Intermediate Similarity	NPD7778	Approved
0.7182	Intermediate Similarity	NPD53	Approved
0.7166	Intermediate Similarity	NPD7859	Phase 2
0.7164	Intermediate Similarity	NPD8279	Clinical (unspecified phase)
0.7163	Intermediate Similarity	NPD3961	Discontinued
0.7161	Intermediate Similarity	NPD7710	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD1304	Clinical (unspecified phase)
0.7156	Intermediate Similarity	NPD7222	Phase 2
0.7149	Intermediate Similarity	NPD3814	Phase 1
0.7149	Intermediate Similarity	NPD3330	Phase 1
0.7143	Intermediate Similarity	NPD8109	Clinical (unspecified phase)
0.7137	Intermediate Similarity	NPD8463	Approved
0.7124	Intermediate Similarity	NPD2510	Approved
0.7124	Intermediate Similarity	NPD2509	Approved
0.7119	Intermediate Similarity	NPD4086	Phase 1
0.7117	Intermediate Similarity	NPD8248	Clinical (unspecified phase)
0.7109	Intermediate Similarity	NPD6159	Phase 2
0.7091	Intermediate Similarity	NPD7818	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD8525	Approved
0.708	Intermediate Similarity	NPD7452	Approved
0.708	Intermediate Similarity	NPD7453	Approved
0.707	Intermediate Similarity	NPD8364	Approved
0.707	Intermediate Similarity	NPD8363	Approved
0.7063	Intermediate Similarity	NPD6531	Approved
0.7063	Intermediate Similarity	NPD6530	Approved
0.7061	Intermediate Similarity	NPD8460	Approved
0.7061	Intermediate Similarity	NPD8459	Approved
0.7061	Intermediate Similarity	NPD7921	Approved
0.7059	Intermediate Similarity	NPD6664	Approved
0.7056	Intermediate Similarity	NPD7112	Discontinued
0.7047	Intermediate Similarity	NPD6456	Discontinued
0.7046	Intermediate Similarity	NPD7994	Phase 2
0.7045	Intermediate Similarity	NPD4558	Phase 2
0.7042	Intermediate Similarity	NPD7415	Suspended
0.7037	Intermediate Similarity	NPD2921	Clinical (unspecified phase)
0.7031	Intermediate Similarity	NPD5066	Phase 2
0.7031	Intermediate Similarity	NPD5067	Phase 2
0.7025	Intermediate Similarity	NPD4958	Clinical (unspecified phase)
0.7016	Intermediate Similarity	NPD8365	Clinical (unspecified phase)
0.7012	Intermediate Similarity	NPD8255	Phase 2
0.7009	Intermediate Similarity	NPD7817	Phase 1
0.7004	Intermediate Similarity	NPD1392	Approved
0.7004	Intermediate Similarity	NPD8358	Approved
0.7	Intermediate Similarity	NPD4852	Phase 2
0.7	Intermediate Similarity	NPD3746	Discontinued
0.6996	Remote Similarity	NPD7878	Phase 2
0.6992	Remote Similarity	NPD7717	Approved
0.6992	Remote Similarity	NPD7716	Approved
0.6991	Remote Similarity	NPD8098	Approved
0.6987	Remote Similarity	NPD7589	Clinical (unspecified phase)
0.6987	Remote Similarity	NPD5801	Clinical (unspecified phase)
0.6986	Remote Similarity	NPD6180	Clinical (unspecified phase)
0.6983	Remote Similarity	NPD3393	Approved
0.6983	Remote Similarity	NPD3394	Approved
0.6983	Remote Similarity	NPD3006	Discontinued
0.6983	Remote Similarity	NPD3389	Approved
0.6982	Remote Similarity	NPD5003	Discontinued
0.698	Remote Similarity	NPD6517	Phase 3
0.698	Remote Similarity	NPD3914	Clinical (unspecified phase)
0.6975	Remote Similarity	NPD7268	Clinical (unspecified phase)
0.6974	Remote Similarity	NPD5658	Approved
0.6973	Remote Similarity	NPD8428	Approved
0.6973	Remote Similarity	NPD8466	Approved
0.6973	Remote Similarity	NPD8465	Approved
0.6973	Remote Similarity	NPD8427	Approved
0.6973	Remote Similarity	NPD8429	Approved
0.6973	Remote Similarity	NPD8467	Approved
0.6966	Remote Similarity	NPD7194	Discontinued
0.6964	Remote Similarity	NPD8359	Phase 2
0.6963	Remote Similarity	NPD6452	Discontinued
0.6962	Remote Similarity	NPD7586	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD7655	Discontinued
0.696	Remote Similarity	NPD8403	Phase 1
0.696	Remote Similarity	NPD3003	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data